The role of the Chief Learning Officer (CLO) has evolved considerably over the past decade. Once a more isolated function, employee learning and development has now become a strategic driver of business growth.

In response to this change, the CLO’s position has become more important and more complex. With the nature of work rapidly changing, CLOs must stay ahead of the industry-wide challenges that continue to emerge.

In this article, we’ll look at the main challenges that CLOs are facing in 2025 and explore how these trends might shape the future of learning and development.

Key challenges for Chief Learning Officers in 2025

As the impact of L&D on business outcomes has evolved, so have the challenges that CLOs need to solve in order to broaden L&D’s reach within the business and ensure that those initiatives are effective. 

Learning and development drives both talent and business outcomes, but many organizations have yet to accept the full reach of L&D’s impact. It’s up to Chief Learning Officers to make the business case for learning and development initiatives and demonstrate how these efforts are creating measurable business value. 

The key lies in programs that prioritize practical application, translating knowledge into performance that directly impacts organizational goals.

Declining labor supply and skills-mismatch

Attracting and retaining talent continue to be top priorities for organizations, especially as talent shortages affect various industries, including healthcare, manufacturing, hospitality, and restaurant/food services.


This widespread labor shortage is in part caused by a mismatch between the skills that workers currently have and the skills that employers need the most. Recent research shows that 28% of the time people are getting a certificate or an associate degree in an area where there’s no job for them. 

Learning executives need to think strategically about how to fill critical roles from within, how to retain employees longer, and how to build an employer brand that attracts high-quality talent in order to fill the skills gaps and combat these talent shortages.

Businesses only reap the benefits of learning and development if employees actually take advantage of them. At the same time, many organizations still rely on outdated education programs— such as tuition reimbursement—that are inaccessible to the average worker, resulting in low participation rates.

Outcome-driven CLOs must evaluate whether their existing L&D programs are accessible to the employee populations that need skills development the most. If the answer is no, consider reallocating those resources to a more modern workforce education program that has as wide a reach as possible.

The modern workplace is defined by volatility, complexity, and ambiguity, making it essential for leaders to navigate change with agility and resilience. Truly effective leadership demands a well-rounded skill set, combining self-awareness, interpersonal mastery, strategic business acumen, and strong organizational leadership abilities.

For learning executives, the challenge lies in identifying and implementing leadership development programs that not only build these critical skills, but also equip leaders to thrive in increasingly complex and dynamic business landscapes.

The need for personalized and contextualized learning

There’s a growing need to figure out how to deliver learning experiences that feel personalized to the employee and applicable to their current role, or even a future role they might take on within the organization.

Providing a variety of courses and programs to suit different skills needs across different roles within the business. One-size-fits-all learning solutions won’t work across the board; a frontline retail employee will need vastly different learning than a mid-level IT specialist, for example.

Presenting learning to employees in a way that helps them understand how it will help them advance their career goals. Employees want to know that learning will pay off before they participate and commit to a program. 

Determining how to help learners instantly apply what they’ve learned to their jobs. Chief Learning Officers can work with people managers to determine how to achieve this so that there’s a direct alignment between learning and job performance. 

One of the newest challenges for CLOs is the rise of AI and its impact on the workplace. AI adoption has accelerated somewhat unevenly, with frontline workers being left behind as AI is implemented into the workforce. 

To ensure that all workers are up to speed with the adoption of AI, Chief Learning Officers must ensure that their learning solutions include robust AI upskilling options for workers across all roles. 

The new Chief Learning Officers on the block

As the workforce evolves, so must the role of Chief Learning Officer to ensure that an organization’s learning strategies are directly aligned to its people and business outcomes. The new and evolved CLO role must be poised to meet today and tomorrow’s workforce challenges. 

Looking for more workforce trends? InStride surveyed 1000+ U.S. workers to learn what they really think about employer-sponsored learning programs. Download the report for the full round up of our findings.

Breaking down the top challenges for Chief Learning Officers in 2025, including tackling skills gaps, leadership development, and AI upskilling.

The 5 most pressing challenges for Chief Learning Officers in 2025

Change and adaptation are the only constants for businesses today. Transformations can be big or small—either way, your workforce will play a major role. It’s critical for L&D and HR leaders to recognize this fact and ensure that they’re involved in managing these changes.

The key to doing so is putting learning and development at the core of your organizational transformation so that employee learning is aligned with your changes. 

We’ll look at how L&D can shape organizational transformation in a way that creates alignment between your workforce and your business goals. 

Organizational transformation is the process of making changes to ensure that your organization is aligned with its strategic goals. 

Organizational change can be proactive or reactive, is driven by both internal and external factors, and can take many different forms:

Making a cultural shift (e.g. mergers and acquisitions, return to office mandates)

Implementing a new technology (e.g. digitizing some or all of your existing processes)

Changing to a different business model (e.g. switching from an online business to brick and mortar)

The role of learning in organizational transformation

The success of your organizational transformation depends on the participation and readiness of your employees. Here are four ways that learning and development aligns your workforce to the transformation:

Aligns employee skills and capabilities to business goals

Learning and development equips employees with the skills and capabilities they need to meet the demands of the business. Naturally, as your organization changes, so might their skills needs. L&D helps you address skills gaps during periods of change and proactively plan for future skills needs.

Prepares leaders for navigating change and ambiguity

Successful organization transformation requires strong leadership at all levels. An effective leadership development program can help managers and executives build the skills to lead through uncertainty and successfully manage change.

There are many short-term benefits to learning and development during periods of change, such as immediate upskilling. There’s also long-term potential to help you build a more agile workforce overall. Organizational transformation is rarely a one-time event, and for many businesses where this is an ongoing need, L&D helps you foster a culture of continuous learning.

Change can be uncomfortable, often leading to uncertainty, low morale, or even turnover. A strong L&D foundation addresses these challenges by equipping employees with the skills, resources, and confidence to adapt to new circumstances. 

Additionally, training that’s designed to support change initiatives fosters a sense of stability and demonstrates that the organization values and invests in its people. This support not only enhances employee engagement but also empowers individuals to become advocates for the change, helping to drive a smoother transition.

3 key best practices for enabling organizational transformation with learning

It isn’t enough to simply implement a learning initiative; to truly drive transformation within your org, your initiatives should follow these best practices: 

Your learning initiatives should be aligned strategically with whatever transformation your company hopes to make. The programs, content, and delivery methods should support specific end goals tied to the changes that are taking place. Assessing your initiatives with your goals in mind also gives you an opportunity to re-evaluate and optimize existing initiatives.

Your learning initiatives should be tailored to meet the needs and goals of the employees they are designed for. This means they must be accessible and aligned with employees’ long-term career aspirations.

Learning should also lead to tangible benefits for employees, such as opportunities for advancement and promotion. To drive transformation, you need your workforce to not only build their skills but also stay engaged and committed to the organization’s success.

Learning should never be treated as a one-off solution. Change is inevitable, whether gradual or sudden, and the more comfortable your employees are with continuous learning and skill-building, the easier it will be to foster transformation when the time comes.

Examples of how L&D can shape organizational transformation

Let’s take a couple of common examples of organizational change and see where learning and development fits into the picture.

Changing hierarchy and introducing new roles within the company

Learning and development programs can proactively support succession planning and building internal talent pipelines for leadership roles. During significant changes in company leadership or the creation of new, advanced roles, these programs help ensure smooth transitions by preparing the right employees to take on these roles well in advance.

Advancing diversity, equity and inclusion 

Furthering diversity, equity, and inclusion (DEI) initiatives is an example of organizational transformation that’s both strategic and cultural. The most immediate application of L&D in this example is developing DEI training for your workforce, but there are also long-term benefits beyond this.

Historically, people from underrepresented groups often face systemic barriers to education. By providing access to learning and debt-free education, businesses are in a unique position to break down these barriers and help individuals go back to school, take on advanced degrees, and build skills that make them eligible for advanced positions.

Learning is the key to successful organizational transformation

Organizational transformations are inevitable for businesses that adapt to changing times. But rather than letting these changes unfold without guidance, consider how a strategically aligned learning initiative can guide your workforce through these changes and lead to a more agile, adaptable workplace. 


Want to dive into more L&D resources? Check out this guide for tips on how to build an effective skill-building program that supports organizational transformation.

Organizational transformation thrives on effective employee learning and development. Discover how L&D supports organizational change.

Why you can’t drive organizational transformation without L&D

Best practices to enable organizational change with L&D

Examples of L&D shaping organizational transformation

Organizations committed to positive change in today’s working culture are taking action-oriented steps toward better diversity, equity and inclusion (DEI) practices. Diversity in the workplace is already a familiar concept to forward-thinking companies. But in recent years, increased awareness around social exclusions faced by people from marginalized backgrounds has prompted the term “equity” to be at the forefront of conversations around diversity and inclusion.

As business leaders continue to strategize how to foster a culture of belonging among their employees, they must add the idea of workplace equity to their leadership toolkit.

In this article, we’ll discuss the meaning of equity, why it’s important and how you can build an equitable working environment for your employees.

Workplace equity is the concept of providing fair opportunities for all of your employees based on their individual needs. Before we dive into the details of what this looks like in practice,  let's run through a couple of important definitions.

Although equity and equality sound similar, they are not synonymous. To properly plan for a more equitable workplace, it's important to have a strong understanding of how these terms differ.

Equality seeks to provide all employees with access to the same resources, regardless of the pre-existing barriers they may face. This can refer to an equal distribution of money, resources or opportunities between workers at a similar level. 

Equality is in many ways a beneficial concept that can push company culture in the right direction. However, it often fails to address problems of underrepresentation or an unfair status quo.

Equity is distinct from equality in that it doesn’t provide the same resources and opportunities to everyone. With equity, an organization will recognize that each employee has varying access to resources and privileges. And those with less access may need more support to take fair advantage of opportunities within a given company.

Equity can be complicated to demonstrate in the workplace. This is because what constitutes fair and equitable treatment is often subjective and unique to the experiences of every individual employee.

However, an organization can show equity in the workplace by first recognizing this reality. Fostering an equitable workplace begins with cultivating a safe environment that allows for open discussion and understanding. We’ll talk more about specific steps to take towards equity in the next section.

Equity in the workplace is about “leveling the playing field,” and giving every employee the unique resources they need to have access to opportunities at a given organization. Here are a few ways you can implement a practice of equity within your company.

Prioritize wage equity
Discussion of wages has been made taboo in the past, however, this allows bias in the form of wage disparities to slip through the cracks. Having transparency around wages and openly discussing correlations between employee performance, position and rate of pay are essential to ensuring fair compensation.

Ensure diverse cross-level representation
Many organizations hire for diversity but fail to provide equitable opportunities for advancement to their diverse hires. When this happens, what we see is high diversity in low-paying and low-authority jobs, and over (or exclusive) representation of one demographic in leadership and management. Your company should empower diverse employees by giving equitable promotions and upholding diverse representation in executive positions.

Invest in workforce education
Systemic barriers prevent especially Black, Indigenous and people of color (BIPOC), as well as disabled individuals from accessing education. This lack of access creates an enormous diversity deficit in many workplaces. By investing in a workforce education program, you’re providing your marginalized employees with a potentially life-changing resource that enables them to advance their careers and grow with your company. Fair education is the key to an equitable future in the workplace.
 

Here are seven examples of how you can enable an equitable working environment.

Make job descriptions accessible
This means having transparency around the wage range for different positions, as well as providing a variety of avenues through which talent may access application materials (including non-web-based channels).

Shift to skills-based hiring
Not everyone has access to higher education and this shouldn’t bar them from opportunities for work if they have the skills necessary to do the job. This is the gist of skills-based hiring. Instead of focusing on specific degree requirements in your hiring process, emphasize skills and previous work experience. Then, leverage your existing L&D resources to upskill and reskill these individuals for continuous career advancement.

Provide inclusive incentives
Event-based incentives that center around alcohol or formal dress codes have the potential to alienate some employees. Financial or recognition-based incentives are a better way to reward top-performing team members and avoid exclusion.

Provide equitable access for all employees
This not only means access to resources and opportunities but also physical spaces and materials. It is important to consider whether your meeting room is wheelchair-friendly, whether you have accurate closed captions on a video presentation, and whether your office space has adequate accommodations for employees with sensory sensitivities.

Empower your employees
Even if you have all the best resources in place, it’s up to your employees to take advantage of them. For you, this means making sure your employees know about the resources, know how to access them and feel comfortable and safe doing so.

Ensure equitable benefits
Spousal health insurance should be available to same-sex couples and non-traditional families as well as straight couples. Additionally, parental leave should extend to fathers and mothers equally.

Re-evaluate your equity practices
Everyone makes mistakes and as we continue to take action against a problematic status quo it can be difficult to know what’s right. Organizations should continue to analyze and update their equity practices as new information is given.
 

There's no surefire method for accurately measuring equity in the workplace, which makes it challenging to know the impact of your efforts. A common tactic for understanding the state of equity in your organization is through employee satisfaction surveys or net promoter scores (NPS).

Here's an example of some survey questions you can include that specifically speak to equity:

Do you believe you are treated fairly at work?

Do you believe that your organization's promotion practices are fair?

Do you believe that your compensation and benefits package is fair for your skills, level of experience and job responsibilities?

Additionally, it's important to collaborate closely with your people management team and train them on how to have open conversations about DEI with their direct reports. Managers are in a unique position to build trust with their teams and solicit honest feedback.

Equity, the practice of meeting the unique needs of individual employees, is a vital concept for today’s workforce. Implementing equitable actions in your organization has the potential to change the lives of your employees and affect positive change in the wider world.

Ready to take greater action on DEI? Download this free diversity presentation template to access industry benchmarks, project roadmaps and other useful tools to power your DEI strategy forward.

Don't overlook the importance of equity. Here are 7 exceptional examples of promoting workplace equity to guide your DEI strategy.

7 exceptional examples of equity in the workplace

Don't overlook the importance of equity when developing a DEI strategy. Here are 7 examples of equity in the workplace to guide your efforts.

Action Behavior Centers exceeds promotion rate goals on 3-year anniversary of employee education program

Calculate the return-on-investment with InStride for your industry with this easy-to-use ROI calculator.

ROI Calculator | InStride

From Retail to Finance, InStride helps industries of all types achieve up to a 300% return on their education investments. Want to see your actual ROI and get an in-depth analysis?

EVP Human Resources, Aramark

InStride brings together top-tier educational institutions that have tried and tested online learning. We carefully curate a combination of education programs to meet the future needs of the workforce.

Most workforce education programs lack strategic design

Whether it’s out of reach or uneffective, traditional tuition assistance programs still fall flat. See how we’re changing this for good.

InStride is the premier global provider of strategic enterprise education for companies that need to align their talent & workforce needs with business objectives.

Calculate your potential ROI with strategic workforce education

Companies making an impact

“We are committed to making this program as easy as possible for employees to access. This means removing possible barriers to entry and providing the support they need at each step of their educational journey.”

A better step forward